We have similar music tastes: I'm also a bass-head and avoid sharp trebel; I don't listen to R&B, but plenty of hip-hop. So my thoughts should line up well with your experience.

Open Back Open back is superior in every way. Some say closed back are better for monster bass, which I suppose is possible. I've never bought any audiophile-grade closed backs, so I can't comment. But I have several open backs that more than hold their own with a Beats, even for a bass-head. There's a reason the vast majority of audiophile headphones are open back.

I've never found any open backs in wireless. I'm told it's because there's just no demand for it. The Airpod Max is the closest "quality" headphone I have that's wireless and "open"; but it's not really open from a music perspective, just from a environment/transparency perspective. If you want the best sound wirelessly, your only options are really the Airpod Max or the Focal Bathys.

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There's a lot of snakeoil going on in the community, so let me share my thoughts...

EQ EQ is the best-kept secret in audio. I dont' mean the 6-band EQ that spotify offers; I mean full fidelity EQ settings made by professionals with expensive equipment tailored to a specific set of headphones. For whatever reason, most audiophile headphones don't come with a great tuning; it's almost like they expect you to EQ them. So, if you just take a fresh pair and plug them in, they sound worse than basically any high-end commerical pair you buy off the streets (e.g., the Airpod Max). Some brands are worse than others, but I consider EQ a must. How you get that EQ delivered depends on where you listen to your music:

• iOS: Unfortunately, I haven't found a way to get proper EQ on iOS. The OS doesn't support a system-level EQ, so you're limited to what your player (i.e., Spotify) has built-in. If you plan to go the audiophile route, I don't recommend listening from iOS, which includes iPad.
• MacOS: Get https://rogueamoeba.com/soundsource/. It's not free, but worth every penny. It has presets for all the published "professional" EQ settings.
• Windows: https://github.com/h39s/AQUA. It's free, and a UI built on top of EqualizerAPO. Since it's free, it takes a litte effort to learn how to use it ;) But it works quite well. Since I've been at Microsoft, this is the setup I've been using.

DAC/Amp Definitions, just to be clear. A DAC is the thing that turns digital audio (1s and 0s) into a physical audio wave. An amp is the thing that make a physical audio wave bigger :)

After much experimentation, I have yet to experience a real difference in quality from any DAC or AMP combination. I've never had a headphone "come alive" when using a better DAC or Amp. I do have two caveats:

1. Tube amplifiers are actually a little warmer. People swear some headphones combine really well with tube amps, or that vinyl sounds better on tube amps... I have a tube amp, and it is warmer, but it's a neglegable difference overall.
2. Every device that can play audio via a headphone has an amp. If you go cheap enough - and I mean $2 Temu cheap - I guess it's theoretically possible you could get an amp bad enough. I pretty well guarantee any device you have, especially if it's made by Apple, has a good amp. Whether that amp is strong enough is up to you. Headphones have impedance, which defines how much power they need. If you have a very high impedance headphone (like the Sennheiser 800S, which is 300 Ohm), you won't be able to listen to them very loud straight off your computer. I do recommend an amp for this reason and for the reasons that follow.

The biggest advantage that a DAC and AMP offer is convenience and options. They have varying inputs/outputs and physical controls. I like having a physical volume knob. I like having my headphones plug in within reach, regardless of where my computer is (which is a long way away since I upgraded to a 57" ultrawide monitor). My DAC can switch inputs with a button; I have both my computer and turntable connected to it, so switching is easy. I'll say this again later, but I also just like having cool, high-quality products; don't overlook the satisfaction this provides, even if you can't explain why. My DAC/AMP/EQ (yes, I have a physical EQ too, lol) all come from https://www.schiit.com/. I have the Modius (DAC), Magnius (Amp, which I believe is the Midgard now), and the Lokius (EQ). I recommend Schiit, but I can help pick out some other stuff if you decide to go this route too.

Headphones In general, you get what you pay for. However, there are significant diminishing returns after ~$500. There are two kind of headphones: dynamic, and planar; this refers to the actual driver that produces the audio. Most commercial headphones - in fact, probably all of them - are dynamic; there's nothing wrong with dynamic drivers. Planars typically take a little more power to drive and have a little punchier (think faster, not necessarily more) bass; typically... but the differences are quite small by comparison. Unless you plan on starting a collection like yours truely, I wouldn't let this distinction matter.

Aside from the driver type, the biggest difference is in looks, build quality/materials, and weight. Some audiophile headphones can get HEAVY; my lightest are 9oz, and my heaviest are 1.35lbs. If that's a concern, just be aware.

I'm going to list headphones I have in order of my recommendation; best first.

• Sennheiser 660S ($450) - If you read r/headphones at all, you'll likely come across these juggernauts. The reputation is justified. EQ is 1000% necessary, more than any other headphones I've ever listened to. But it's worth it. They are often critiqued for their lack of bass, which is justified ON THE DEFAULT TUNING; they are very capable in the bass department with proper EQ. But the reason they stand out... is the mids. I know that sounds odd, because no one knowing likes mids. It's something you will just have to experience. No other heapdhone at any price point has better mids. They're often described as "smooth" and "buttery", which is rediculous, but also pretty accurate :) You'll know what I mean if you every try them. The down-side is, these headphones are made of mostly plastic. They have a classic headphone look to them, but kind of like the Honda of headphones from a looks department. However, they are extremely light weight and disappear on your head. These are the lightest headphones I have. I think the 600S is no longer being sold, so you'd have to buy them used or get the 660S2 which is the newer model. I haven't tried them personally, but I hear they are similar to the 660S, but a little warmer, which is good for you.
• Focal Clear ($800) - These are the best audiophile headphones in their default tuning. Before I discovered EQ, these were my favorite. They are quite warm, which I think you'll like. They're made in France with high quality metal/leather. They weigh 16oz, so middle of the road. They are pretty easy to drive.
• Meze Empyrean ($3,000) - These are half headphone, half a work of art. The craftsmanship, materials, design are second to none. There's no plastic anywhere on the device; it's either metal, leather, or carbon fiber. Every single piece is servicable. At the very least, you should look at them :) They weigh 14oz, so middle of the road. They might be the most pair of headphones ever, which is kind of their reputation. Sound-wise they are as amazing as you'd expect for the price tag. Like I said, there's diminishing returns and they hit hard here. Are they better than the 660S? Probably. The mids aren't. But overall they are probably marginally better. These excel at layering music, largly in part to the unique (and patented) design of their planar driver. Unless you just have money to throw around, and want these art pieces, you should get the Sennheisers. However, these are my daily drivers and I love them.
• Audeze LCD-X ($1,200) - These are high-quality, industrial-build bass monsters. They are heavy; at 1.35lbs, they are noticably heavier than pretty much everything else I have. Despite them being bass monsters, I don't use mine. The others I've recommended have more than enough bass and excel at other areas, so these just don't get the seat time anymore. They are pretty fantastic headphones though.

Pads Pads wear out; it's a fact of life. https://dekoniaudio.com/ makes pads for pretty much everything. The pad material can marginally change the sound. Leather is warmer than microfiber. I have fenestrated sheep skin pads for all my headphones. Once you've settled on a pair you like, I recommend this.

Cables I have custom cables for all my headphones. Mostly from https://oidiosound.co.uk/, but also some from https://hartaudiocables.com/ and https://periaptcables.com/. I've been on a woven kick latley, so I'm hooked on their https://oidiosound.co.uk/mongrel-3pin-minixlr?search=Mongrel%20Cable cable. Cables do NOT change the audio quality. Again, this is mostly for looks/convenience/I-like-them-ok.

That should cover it :)